Bozhanov V. 4-Heteryl(aryl)-2,3-dihydro-1H-1,5-benzodiazepin-2-ones. Synthesis and reactivity

Object of investigation: 2,3-dihydro-1H-1,5-benzodiazepin-2-ones. Aim of investigation: synthesys of new 2,3-dihydro-1H-1,5-benzodiazepin-2-ones with heteryl and aryl substitutents has been carried out, their reactivity with electrophilic and nucleophilic reagents. Methods of investigation and instruments: organic synthesis, IR-, UV-, NMR-spectroscopy, mass spectrometry, elemental analysis, chromatography. Theoretical results and novelty: It is shown that the esters of 3-substituted acrylic acid or 4-heteryl- 2,3-dihydro-1H-1,5-benzodiazepin-2-ones have been obtained in dependency on electronic character of substitutent b-ketoester and o-diamine and reaction conditions. The isomeric 7- or 8-R-4-heterylbenzodiazepinones have been obtained for nonsymmetrical o-phenylendiamines. The reactivity of 4-heteryl(aryl)-2,3-dihydro-1H- 1,5-benzodiazepin-2-ones has been investigated in the electrophilic reactions: alkylation, halogenation, aminoalkilation. The 3-substituted 1,5-benzodiazepinones have been obtained from 3-bromobenzodiazepinones and various N- and S- nucleophiles. It was shown that rearrangement of dihydrobenzodiazepinones into benzimidazolones depended on substitutent in 3 and 4 positions of heterocyclic system. Practical results and novelty: Нave been obtained over 70 of new 2,3-dihydro-1H-1,5-benzodiazepin-2-ones. Working out the metodies of synthesis of 4-heteryl(aryl)-2,3-dihydro-1H-1,5-benzodiazepin-2-ones and the way of modification 1,5-benzodiazepines cycle. Subject and degree of in-troduction: publications, reports on scientifics conferences, application of present work results in scientific and education practice in universities and institutes of Ukraine. Field of application: chemistry, industry.